Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (±)-3a,3a'-bispyrrolo[2,3-b]indoles

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概要

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• A unique synthetic method for melatonin was established through biologically promising synthetic intermediates. 1-Hydroxymelatonin was prepared as crystals for the first time. It reacted with 85% formic acid to give (±)-3a,3a'-bispyrrolo[2,3-b]indole compound, whose structure was unequivocally determined by X-Ray crystallographic analysis

• 日本複素環化学研究所の論文

著者

• 長谷川 雅司

  Exploratory Research Laboratories Iii Daiichi Pharmaceutical Co. Ltd.

• Hasegawa M

  Faculty Of Pharmaceutical Sciences Kanazawa University

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• The Chemistry of Indoles.CIII.^ Simple Syntheses of Serotonin, N-Methylserotonin, Bufotenine, 5-Methoxy-N-methyltryptamine, Bufobutanoic Acid, N-(Indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and Lespedamine Based on 1-Hydroxyindole Chemistry
• The first total synthesis of bufobutanoic acid by two routes based on nucleophilic substitution reaction on indole nucleus
• Novel formations of 6-mesyloxytryptamines and 1-substituted 3a-(4- chlorobutoxy)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles in the reaction of nb-substituted 1-hydroxytryptamines with mesyl chloride
• Syntheses of melatonin and its derivatives
• A novel methodology for preparing 5-chloro- and 5-bromotryptamines and tryptophans, and its application to the synthesis of (±)-bromochelonin B
• Preparations of melatonin and 1-hydroxymelatonin, and its novel nucleophilic dimerization to (±)-3a,3a'-bispyrrolo[2,3-b]indoles

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